“Trust yourself, stay true to your vision, and design/create from a place of authenticity” with Dinah Chapman
Photo credit: Little Trouble
Dinah Chapman is the founder of Little Trouble, the kids' fashion brand that flipped the script on boring boys' clothes. What started as a pandemic passion project quickly went viral, and now Dinah's designing from Bali, making clothes that bring out the rebel in every little one. She’s here to shake up the fashion world and make sure your kids look cooler than you ever did.
Photo credit: Little Trouble
Can you tell our readers about your background?
I’ve been working in e-commerce and digital marketing for about 12 years. I started in fashion before transitioning into skincare, where I led the strategic growth of a company, driving multi-million-dollar revenue expansion in under five years. During this time, I also started Little Trouble, driven by my personal frustrations with the lack of stylish boys' clothing.
What inspired you to start your business?
I was pregnant with my first son and was so frustrated while shopping for clothes. There were so many cute options for girls, even some alternative stuff but for boys…nothing. I was looking for cool, somewhat edgy styles that fit my personal style aesthetic and just kept coming up short. That’s when I decided I was going to give it a shot and do it myself, hoping there were other parents like me who would like what I liked. I already had a background in fashion and marketing, so it felt like the right time to bring something fresh to the market.
Where is your business based?
My business was founded and is based in the States but I’m currently living in and running the business from Bali. We moved here for a change of pace, better proximity to our manufacturers, and it just made sense for our lifestyle. The time zone’s perfect for coordinating with our global team, and the creative energy is unmatched. Plus, who doesn’t want to live in Bali, right?
How did you start your business? What were the first steps you took?
I started Little Trouble as a side hustle, honestly thinking it would be a small Etsy-style project. My husband and I put all our savings into it, and I began designing clothes while still working full-time at a skincare company. After we launched, I quickly sold out of hoodies – in the middle of a California heatwave, no less. That’s when I knew we had something good. The brand took off from there, and we went from garage operations to full-on warehouse life.
What has been the most effective way of raising awareness for your business?
Social media has been a game-changer. Instagram and TikTok helped us reach moms who felt the same frustration I did. Our TikTok success, especially with our "Punkhoodi" hoodie, was huge. We sold thousands of units, and being the first kids’ brand on TikTok Shop made a massive impact. It went viral and got us a ton of organic traction.
What have been your biggest challenges and how did you overcome them?
Scaling was the hardest part – especially when you’re working out of your garage and dealing with a newborn. We quickly outgrew our space and had to hustle to make room for growing inventory. There was a lot of sleepless nights, but I leaned on the support of my family and kept pushing forward. Eventually, we moved to a warehouse and grew from there. It wasn’t easy, but when things got tough, we just kept innovating and working smarter.
How do you stay focused?
I stay focused by reminding myself why I started. The community we’ve built around Little Trouble is everything. I’m deeply connected to the moms who follow us, and I never forget that the reason this brand exists is because we’ve created something real for them. Also, I’m not afraid to admit when I need to step back and delegate. I’ve learned that running a business means letting go of perfection sometimes.
How do you differentiate your business from the competition?
I focus on designing clothes that are authentic to my family's lifestyle and my kids’ ages. Staying on trend is important for market appeal no doubt but making sure the designs have character and true attention to even the smallest details is what sets Little Trouble apart from other kids brands selling the same patterns and generic graphics. I design things my older son Cash will love. He is my market tester. He often chooses final colors, materials, prints etc. and I trust him because he’s giving the most genuine and pure feedback based on what he loves at the current moment which I’ve learned (according to the sales) tons of other kids his age agree with!
What has been your most effective marketing strategy to grow your business?
Gifting and networking on my organic socials. Finding mommy bloggers, creators, and influencers who had little kids or were expecting and just starting conversations to ultimately send them packages for their kids to enjoy. Parenting, and even more specifically motherhood, is an easy thing to bond over, so it made connecting much easier. My gifting and partnership strategy has always been really low-stress and casual. I want people to genuinely enjoy the clothing and then either create content or give me a tag and shoutout if they want to and it feels natural for them. My end goal is to get as many people wearing and looking at Little Trouble as possible and while social media call outs are huge for propelling my business forward, word of mouth and knowing people are wearing my Fool For Fuel Hoodie at Monster Jam or my Checker Overalls at birthday parties is huge for localized marketing and community building.
What's your best piece of advice for aspiring and new entrepreneurs?
Trust yourself, stay true to your vision, and design/create from a place of authenticity. You don’t have to wait for everything to be perfect – the best lessons are learned through experience. Things get hard before they get really good.
What's your favorite app, blog, and book? Why?
Honestly, I don’t have time for many books or blogs in this season of my life. We’re listening to Danny Go or Lenny Pearce who makes a pretty epic techno version of Wheels on the Bus. The house is never silent and I could crush the excavator song during karaoke.
What's your favorite business tool or resource? Why?
My current favorite tool is Motion App since I spend a huge amount of time creating, analysing, and iterating ads to scale my busines,s and they have the most amazing UI/UX and features.
Who is your business role model? Why?
Female founders who have made either a major impact in a male-dominated industry or have created really creative brands or visions like Kristy Campbell and Whitney Wolfe.
How do you balance work and life?
I take a movement break daily, which has been an actual life and sanity saver, and I have a no-phone rule (unless I have a pre-scheduled meeting) between 5:30 and bedtime with my kids. There is also one weekend day where, if I have to work, it has to be during nap so that my kids get my full attention. They love to tell me to stop working and close my computer haha.
What’s your favorite way to decompress?
Romance novel and a glass of wine after pilates. Art projects with my kids. If I want to torture myself at all, a cold plunge.
What do you have planned for the next six months?
We’re launching a non-profit initiative called Hugs for Homies where a portion of sales will go directly to help moms and families in need. I want to make sure that every cent goes to where it’s needed most, so this will be super transparent. I’m also continuing to expand the brand and bring more cool products into the mix.
How can our readers connect with you?
Instagram is the best way to connect and see what's happening personally and from a brand perspective!
